Potassium Iodide → 2-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

HRID 1984987ノート

反応式

HRID 1984987 の反応式
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2].Br[CH2:20][CH2:21][CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][CH2:22][S:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2]

参加物

8

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14575314Benzene, 1-[(3-bromopropyl)thio]-4-fluoro-HCID 577188362-Ethyl-6-fluoro-3-piperidin-4-yl-1H-indole

生成物 1

HCID 577188372-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole (0.9 g), 1-(3-Bromo-propylsulfanyl)-4-fluoro-benzene (1.0 g), potassium iodide (20 mg) and potassium carbonate (0.7 g) in DMF (10 ml) is heated at 100° C. for 3 h, and allowed to cool to rt overnight. Ethyl acetate (50 ml) and water (25 ml) are added and the organic phase is washed with water, dried and concentrated in vacuo. The crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt is prepared by reaction in acetone with the appropriate amount of ethereal HCl giving, after recrystallisation from ether, 1.1 g pure product (70%) as white crystals.

後処理

  1. temperatureto cool to rt overnight
  2. washthe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt
  6. customis prepared by reaction in acetone with the appropriate amount of ethereal HCl giving
  7. customafter recrystallisation from ether, 1.1 g pure product (70%) as white crystals

出典と根拠

ORDレコード
ord-098cd65c53954661a1a36fefa5491bb1
出典データセット
uspto-grants-2009_06
特許番号
US07544806B2

反応ノート

読み込み中…